Potassium Carbonate → 1,2,3,5-tetrahydro-a,7-diphenyl-4H-1,4-benzodiazepine-4-acetic acid, methyl ester

HRID 849401Notes

Reaction equation

HRID 849401 reaction equation
Cl.N1C=C(C[N:8]2[C:14]3[CH:15]=[CH:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:18][C:13]=3[CH2:12][N:11](C(C3C4C(=CC=CC=4)C=CC=3)=O)[CH2:10][CH2:9]2)N=C1.C([O-])([O-])=O.[K+].[K+].Br[CH:44]([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:45]([O:47][CH3:48])=[O:46]>CO>[C:49]1([CH:44]([N:11]2[CH2:12][C:13]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:16]=[CH:15][C:14]=3[NH:8][CH2:9][CH2:10]2)[C:45]([O:47][CH3:48])=[O:46])[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 178479668HCID 178479668, compound

Product 1

HCID 867550391,2,3,5-tetrahydro-a,7-diphenyl-4H-1,4-benzodiazepine-4-acetic acid, methyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of Compound B of Example 12 (220 mg, 1.0 mmol) in MeOH in the presence of solid K2CO3 at room temperature under argon was added methyl bromophenylacetate (0.18 mL, 1.1 mmol). The mixture was stirred for 18 h, the solvent was removed, and the residue was purified by flash column chromatography (3:2, hexanes and ethyl acetate) to give 1,2,3,5-tetrahydro-a,7-diphenyl-4H-1,4-benzodiazepine-4-acetic acid, methyl ester as an oil (220 mg, 63%). This material was reacted as described for Compound D of Example 1 to afford Example 222 as a yellow solid.

Workup

  1. customthe solvent was removed
  2. customthe residue was purified by flash column chromatography (3:2, hexanes and ethyl acetate)

Sources & evidence

ORD record
ord-789e5b89983c44e993a645bff9c76c8c
Source dataset
uspto-grants-2000_01
Patent number
US06011029

Reaction notes

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